B9647

(E)-5-(2-Bromovinyl)-2′-deoxyuridine

• Synonym(e): BVdU
• Empirische Formel (Hill-System): C₁₁H₁₃BrN₂O₅
• CAS-Nummer: 69304-47-8
• Molekulargewicht: 333.14
• NACRES: NA.77
• PubChem Substance ID: 24278280
• UNSPSC Code: 12352200
• MDL number: MFCD00058585
• Form: powder

Eigenschaften

• form: powder
• Quality Segment: 200
• storage temp.: 2-8°C
• SMILES string: O=C(C(/C=C/Br)=CN1[C@H]2C[C@H](O)[C@@H](CO)O2)NC1=O
• InChI: 1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1
• InChI key: ODZBBRURCPAEIQ-PIXDULNESA-N
• Gene Information: human ... HV1S(3365)

Beschreibung

Application

(E)-5-(2-Bromovinyl)-2′-deoxyuridine (BVdU) has been used:

• as a substrate for thymidine kinase 1 to study its effects on cancer cells by a dual-promoter integrator approach
• as a bromovinyl nucleoside analog to study its effects on varicella-zoster virus replication in a mouse model
• as a nucleoside analog prodrug to study its effects on transduced cells

Biochem/physiol Actions

(E)-5-(2-Bromovinyl)-2′-deoxyuridine(BVdU) is a thymidine analog and a well-known inhibitor of Herpes simplex virus type 1 (HSV-1) and Varicella zoster virus (VZV) infections. It shows a minimal effect on HSV-2. BVdU shows therapeutic effects against herpetic keratitis, recurrent herpes labialis, and herpes zoster. BVdU undergoes phosphorylation at its 5’-diphosphate and further to 5’-triphosphate by the virus-encoded thymidine kinase, this results in BVdU acting as a competitive inhibitor to the viral DNA polymerase.

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)